4-Cyan-2,2,5,5-tetramethyl-3-imidazolin-1-oxyl | 64918-64-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 4-Cyan-2,2,5,5-tetramethyl-3-imidazolin-1-oxyl
• CAS: 64918-64-5
• 化学式: C₈H₁₂N₃O
• 分子量: 166.203
• InChiKey: BXOVZLNCURKLEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  40.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Cyan-2,2,5,5-tetramethyl-3-imidazolin-1-oxyl 、 1-羟基-2,2,4,5,5-五甲基-3-咪唑啉 在 lithium diisopropyl amide 、 manganese(IV) oxide 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 0.58h， 以90%的产率得到4-[2-(2,2,5,5-tetramethyl-1-oxylimidazolidin-4-ylidene)-1-iminoethyl]-2,2,5,5-tetramethyl-2,5-dihydro-1H-imidazole-1-oxyl
  参考文献：
  名称：

  摘要：

  The reactions of the dianion generated from 1-hydroxy-2,2,4,5,5-pentamethyl-2,5-dihydro-1H-imidazole under the action of lithium diisopropylamide with nitroxyl radicals derived from 2,5-dihydro-1H-imidazole or 2,5-dihydro-1H-imidazole 3-oxide and containing the ester, aldehydo, cyano, or imino groups afforded biradicals, including those containing the enamino ketone and enamino imine functions. The reactions of this dianion with nitriles derived from 2,5-dihydro-1H-imidazole 3-oxide gave rise to all enamino nitrile, i.e., electrophilic cyanation formally occurred.

  DOI：

  10.1023/a:1011364929195
• 作为产物：
  描述：

  在 羟胺 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以35%的产率得到4-Cyan-2,2,5,5-tetramethyl-3-imidazolin-1-oxyl
  参考文献：
  名称：

  Acyl chlorides of 2,2,5,5-tetramethyl-3-imidazolin-1-oxyl-4-0-acylhydroximic acids

  摘要：

  Acylation of nitroenamine derivatives of imidazolidin-1-oxyl with carboxylic acid chlorides leads to O-acylhydroximic acid chloride derivatives of 3-imidazolin-1-oxyl. The reaction proceeds apparently through a nitrile oxide. It was shown for the O-benzoyl derivative that reaction of the obtained acyl chlorides with nucleophilic reagents usually gives products of chlorine atom substitution with simultaneous cleavage of the acyl group.

  DOI：

  10.1007/bf00965436

文献信息

• Heterocyclization Reaction ofα-Imino Carbonyl Compounds− Derivatives of 2,5-Dihydro-1H-imidazole Nitroxides
  作者：Galina A. Roshchupkina、Natalie V. Pervukhina、Tatjana V. Rybalova、Yuri V. Gatilov、Alexey B. Burdukov、Vladimir A. Reznikov

  DOI：10.1002/ejoc.200300212

  日期：2003.11

  α-Imino carbonyl compounds − derivatives of 3-imidazoline nitroxides − were found to undergo heterocyclization reactions, yielding oxazole and 1,3,5-triazine derivatives. The most probable course of the reaction was suggested by the radioactive label method. The structures of the heterocycles synthesized were verified by X-ray analysis of the mixed-ligand complexes with copper hexafluoroacetylacetonate

  α-亚氨基羰基化合物 - 3-咪唑啉氮氧化物的衍生物 - 被发现发生杂环化反应，产生恶唑和 1,3,5-三嗪衍生物。放射性标记法表明了最可能的反应过程。合成的杂环的结构通过与六氟乙酰丙酮酸铜的混合配体配合物的 X 射线分析来验证。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Acyl chlorides of 2,2,5,5-tetramethyl-3-imidazolin-1-oxyl-4-0-acylhydroximic acids
  作者：V. A. Reznikov、L. A. Vishnivetskaya、L. B. Volodarskii

  DOI：10.1007/bf00965436

  日期：1991.2

  Acylation of nitroenamine derivatives of imidazolidin-1-oxyl with carboxylic acid chlorides leads to O-acylhydroximic acid chloride derivatives of 3-imidazolin-1-oxyl. The reaction proceeds apparently through a nitrile oxide. It was shown for the O-benzoyl derivative that reaction of the obtained acyl chlorides with nucleophilic reagents usually gives products of chlorine atom substitution with simultaneous cleavage of the acyl group.
• ——
  作者：V. A. Reznikov

  DOI：10.1023/a:1011364929195

  日期：——

  The reactions of the dianion generated from 1-hydroxy-2,2,4,5,5-pentamethyl-2,5-dihydro-1H-imidazole under the action of lithium diisopropylamide with nitroxyl radicals derived from 2,5-dihydro-1H-imidazole or 2,5-dihydro-1H-imidazole 3-oxide and containing the ester, aldehydo, cyano, or imino groups afforded biradicals, including those containing the enamino ketone and enamino imine functions. The reactions of this dianion with nitriles derived from 2,5-dihydro-1H-imidazole 3-oxide gave rise to all enamino nitrile, i.e., electrophilic cyanation formally occurred.